My First Dress Up With My Neighbor

When I was younger I had already worn pantyhose and silk underwear and wanted more. At the time there was no way for me to purchase the clothes I wanted to wear.

One day in the summer, I noticed my neighbor had her wash hung out on the clothesline. I knew it was wrong to take things that did not belong to me, but the urge to be fully dressed in women's clothes was just too much.
I went out back and sat in my backyard for a few minutes checking things out. There was no one around so I hopped over the fence and went straight to the clothesline. I took the clothes pins off of the silk panties, and the silk nightgown and was unpinning a pretty silk blouse when I heard a voice say, may I help you?
As I looked up I saw my neighbor standing there looking at me with an angry face. She asked me what I was doing. I had no choice but to tell her the truth.
I told her how much I had wanted to wear women's clothes for a very long time and just could not wait any longer.
She told me that I had two choices.
One she would call the police and I would be in a lot of trouble or I could come inside her house and she would explain to me what I had to do to get out of trouble.
This left me little to no choice so I followed her inside. She said you already know that I am going to paddle your ass for you don't you?
I said yes. She said you address me as yes ma'am every time you speak to me. Yes ma'am.
She said wait right here I will be right back.
Yes, I was truly very scared. I knew her as my neighbor but had never really sat and talked to her before.
She returned in no time and in her hand was a wooden paddle. She said take your pants off and your underwear off and bend over the couch right now.
Yes ma'am.
She touched the paddle to my ass and smacked it hard. That hurt. The second one hurt even more and the third one brought tears to my eyes.
She said you never steal from me again.
If you want something you come and ask me.
Understood?
Yes, ma'am and I am so very sorry to you for what I did.
She asked me if I had worn women's clothes before and I told her only panties and pantyhose. I explained I had no way of getting other clothes but I so wanted to wear them.
She said come with me.
She took me to the bathroom where she said to strip and get in the shower. Wash your entire body with soap and when you get out put on this robe and come to my bedroom.
I said yes ma'am as I was so scared of her. I had no idea what she was going to do to me.
As I walked into her bedroom wearing only a silk see-through robe, she said drop the robe and get down on your knees. I was too afraid not to. On my knees, she placed handcuffs and ankle shackles on me and slipped a blindfold over my eyes.
She then took me by my hair and pulled me to the edge of her bed where she placed my head between her legs.
She asked me, do you know how to eat a woman's pussy?
I said no ma'am I had never done that before. She gave me instructions on exactly what I was to do and told me if it was not very good she would paddle my ass again. I worked so hard licking her so good and each time she had an orgasm she told me to lick her clean and swallow it.
I must say I will never forget the sweet taste of strawberries that I found all through her pussy and could not get enough of that. I knew this was what I wanted to do for the rest of my life. In this short time, I had fallen so deeply in love with her that she could have anything she ever wanted and I would do anything she told me to do. I so loved eating her pussy for her. This was the best day of my life!

After what must have been three or four hours she let me stop. She removed the handcuffs and ankle shackles and blindfold. She told me that I was going to dress in her clothes for her and then model them for her. She laid out pink silk panties, pantyhose, a black bra, and very sexy silk lingerie and told me I had better hurry up and get dressed for her.
I was so afraid of her that I got dressed in her clothes just as fast as I could. She said, lay down on your back on my bed in the middle. She told me to raise my arms above my head where she slipped silk ties over my wrists and spread my legs wide open and silk tied them to the bedpost. She got on top of me and asked me, do you know who owns you?
I said yes ma'am I am owned by you.
Yes, and if you ever forget it I will call the police and report you for stealing.
You will do exactly as I tell you to do as I am now your owner.
She then lowered herself onto my face and rode my face having orgasms over and over and telling me to let them run down into my mouth so I could drink her nectar.
We did this for hours and hours.
She untied me and told me to lie on my stomach. She tied me so tight I could not move and placed a ball mouth gag in my mouth.
She then put on a strap-on and took her fingers and put anal lube on them and ran them as far up my ass as she could making me scream.
The mouth gag made it so no one could hear me. She slowly inserted the strap-on into my ass asking me have you ever been fucked before? I said no ma'am I am a virgin. She said when you leave her you won't be a virgin plus you will be owned by me.
We are going to do these things every day.
Can you come over to my house every day to serve me?
Yes ma'am my mom works and I can do as I please. She said you be here each day at eight am and don't be late. You will be here all day long as I enjoy different kinky sex with you. Do you understand me?
Yes ma'am I will do exactly as you say please do not call the police on me.
So every day I pleasured her pussy for hours and hours as she made sure I drank from her and became addicted to her nectar.
I would get so very high when I drank her female hormones. I knew from the very first time she had me drink her cum that it was only a matter of time before I was addicted to it. I did not care, all I wanted and could think of was more, please ma'am, more.
In a month I so looked forward to getting my fix from her. The female hormones made me high as could be and I wanted them more every day.
I even told my mom I was spending the night at a friend's house and I asked my neighbor if she would allow me to drink from her pussy all night long.
She said I could earn that right from here but that I had to work for it.
I told her that I would do anything for that.
She told me she wanted me to kiss her ass for her. Then she said start licking my ass in between my ass cheeks. I spread them open and started licking her and she moaned and said go deeper inside of me, lick my asshole really good, and you can spend the night with me.
This turned me on so much that I got into it big time really licking her tight asshole so good for her. She moaned so loud and even got off to it and told me that was the best job anyone had ever done for her.
She told me that I was now all hers and that she fully owned me.
So I earned a night between her legs eating her pussy all night long and it was the best night of my life!
She dressed me up in different women's clothes every night and had me model them for her. One night she had a girlfriend there and after I modeled for them they tied me down in the bed and did everything you can imagine to me.
I was so in love with both of them and at four am when they took a break I could no longer walk. They had given me something in an enema that made me so high, so horny, so into anything they wanted to do to me and they did everything and more than you can imagine.
This is how I got my start dressing up and you can see why I love it so much today. I have come a long way in my female clothes and makeup techniques and so love being so much a lady and serving my lover in every possible way.
My neighbor did me the biggest favor ever when she caught me that day.
I am so grateful to her and what she did for me.
More sexxy dress-up stories to come.

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